Hydrochloric Acid → HCID 23290097, compound

HRID 1458172Notes

Reaction equation

HRID 1458172 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:18])([F:17])[C:5](=[O:16])[CH2:6][NH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.[OH-].[Na+]>O>[C:8]([NH:7][CH2:6][CH:5]([OH:16])[C:4]([F:18])([F:17])[F:3])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 10657131HCID 10657131, compound

Product 1

HCID 23290097HCID 23290097, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 10 g (0.263 mol) of NaBH4 in 100 ml of H2O was added to 14.8 g (59.4 mmol) of N-(3,3,3-trifluoro-2-oxo-propyl)benzamide in 1000 ml of H2O. After stirring for 2 hours at 25° C., the solution was acidified with concentrated HCl (pH 1), basified by adding NaOH pellets (pH 10) and extracted with AcOEt (3×500 ml). After drying (MgSO4), the organic layer was flash evaporated to give 11 g of a white solid, which was recrystallized from CHCl3 to yield 10.0 g (72%) of pure trifluoromethylalcohol; m.p. 156° C.

Workup

  1. extractionextracted with AcOEt (3×500 ml)
  2. dry with materialAfter drying (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-357346cafadf45aeb10094df715de278
Source dataset
uspto-grants-1998_12
Patent number
US05849866

Reaction notes

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